DE3887039T2 - Azabicyclische Äther. - Google Patents

Azabicyclische Äther.

Info

Publication number: DE3887039T2
Authority: DE; Germany
Prior art keywords: methyl; endo; compound; azabicyclo; octane
Prior art date: 1987-08-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

DE88307113T

Other languages

German (de)

English (en)

Other versions

DE3887039D1 (de

Inventor

Ian Anthony Cliffe

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

John Wyeth and Brother Ltd

Original Assignee

John Wyeth and Brother Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-08-04

Filing date

1988-08-02

Publication date

1994-04-28

1987-08-04 Priority claimed from GB878718444A external-priority patent/GB8718444D0/en

1988-05-20 Priority claimed from GB888811975A external-priority patent/GB8811975D0/en

1988-08-02 Application filed by John Wyeth and Brother Ltd filed Critical John Wyeth and Brother Ltd

1994-02-24 Publication of DE3887039D1 publication Critical patent/DE3887039D1/de

1994-04-28 Application granted granted Critical

1994-04-28 Publication of DE3887039T2 publication Critical patent/DE3887039T2/de

2008-08-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 claims description 59
-1 C3-C5-alkenyl Chemical group 0.000 claims description 35
238000000034 method Methods 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000005518 carboxamido group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
150000001204 N-oxides Chemical class 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000005059 halophenyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
DINZFCLJXXAKOT-UHFFFAOYSA-N N1=C(C=CC2=CC=CC=C12)C1N2CCC(C1OC1C(N3CCC1CC3)C1=NC3=CC=CC=C3C=C1)CC2 Chemical compound N1=C(C=CC2=CC=CC=C12)C1N2CCC(C1OC1C(N3CCC1CC3)C1=NC3=CC=CC=C3C=C1)CC2 DINZFCLJXXAKOT-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 2
FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
125000003396 thiol group Chemical class [H]S* 0.000 claims 1
239000000203 mixture Substances 0.000 description 24
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000007788 liquid Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
239000012312 sodium hydride Substances 0.000 description 13
229910000104 sodium hydride Inorganic materials 0.000 description 13
239000000243 solution Substances 0.000 description 13
QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 11
QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 11
CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 11
239000013078 crystal Substances 0.000 description 10
239000006185 dispersion Substances 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
229910000041 hydrogen chloride Inorganic materials 0.000 description 10
239000004480 active ingredient Substances 0.000 description 9
125000000623 heterocyclic group Chemical group 0.000 description 9
239000000047 product Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000005557 antagonist Substances 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
102000035037 5-HT3 receptors Human genes 0.000 description 5
108091005477 5-HT3 receptors Proteins 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
YLTJVIIEHKBRPA-UHFFFAOYSA-N (6-aminopyridin-2-yl)-(1-methylpiperidin-4-yl)methanone Chemical compound C1CN(C)CCC1C(=O)C1=CC=CC(N)=N1 YLTJVIIEHKBRPA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000003042 antagnostic effect Effects 0.000 description 3
239000006286 aqueous extract Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
230000028161 membrane depolarization Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000004892 pyridazines Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
210000001186 vagus nerve Anatomy 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
LSEAAPGIZCDEEH-UHFFFAOYSA-N 2,6-dichloropyrazine Chemical compound ClC1=CN=CC(Cl)=N1 LSEAAPGIZCDEEH-UHFFFAOYSA-N 0.000 description 1
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 1
GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
KWFFEQXPFFDJER-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)propoxy]aniline Chemical compound C1=CC(N)=CC=C1OCCCOC1=CC=C(N)C=C1 KWFFEQXPFFDJER-UHFFFAOYSA-N 0.000 description 1
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
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241000283973 Oryctolagus cuniculus Species 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
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239000000654 additive Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000004973 alkali metal peroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
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125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
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150000007522 mineralic acids Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
210000001640 nerve ending Anatomy 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000012057 packaged powder Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
CYHOMWAPJJPNMW-RNLVFQAGSA-N pseudotropine Chemical compound C1[C@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-RNLVFQAGSA-N 0.000 description 1
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
150000003216 pyrazines Chemical class 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DE88307113T 1987-08-04 1988-08-02 Azabicyclische Äther. Expired - Fee Related DE3887039T2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB878718444A GB8718444D0 (en)	1987-08-04	1987-08-04	Ethers
GB888811975A GB8811975D0 (en)	1988-05-20	1988-05-20	Ethers

Publications (2)

Publication Number	Publication Date
DE3887039D1 DE3887039D1 (de)	1994-02-24
DE3887039T2 true DE3887039T2 (de)	1994-04-28

Family

ID=26292571

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE88307113T Expired - Fee Related DE3887039T2 (de)	1987-08-04	1988-08-02	Azabicyclische Äther.

Country Status (15)

Country	Link
US (3)	US4929625A (pt)
EP (1)	EP0306148B1 (pt)
JP (1)	JP2711272B2 (pt)
KR (1)	KR970002635B1 (pt)
AU (1)	AU605896B2 (pt)
CA (1)	CA1307790C (pt)
DE (1)	DE3887039T2 (pt)
DK (1)	DK170802B1 (pt)
ES (1)	ES2061660T3 (pt)
FI (1)	FI94250C (pt)
GB (1)	GB2208510B (pt)
HU (1)	HU203348B (pt)
IE (1)	IE61026B1 (pt)
IL (1)	IL87329A (pt)
PT (1)	PT88177B (pt)

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IT1230881B (it) *	1989-06-20	1991-11-08	Angeli Inst Spa	Derivati del r(-) 3-chinuclidinolo
CA2042336A1 (en) *	1990-05-11	1991-11-12	Mitsuo Nagano	Piperidyloxy-and quinuclidinyloxy-isoxazole, derivatives, their preparation and their therapeutic use
YU84791A (sh) *	1990-05-19	1994-06-10	Boehringer Ingelheim Kg.	Biciklicni 1-aza-cikloalkalni
GB9019973D0 (en) *	1990-09-12	1990-10-24	Wyeth John & Brother Ltd	Azabicyclic derivatives
JPH05310732A (ja) *	1992-03-12	1993-11-22	Mitsubishi Kasei Corp	シンノリン−３−カルボン酸誘導体
IL107184A (en) *	1992-10-09	1997-08-14	Abbott Lab	Heterocyclic ether compounds that enhance cognitive function
US5948793A (en) *	1992-10-09	1999-09-07	Abbott Laboratories	3-pyridyloxymethyl heterocyclic ether compounds useful in controlling neurotransmitter release
GB9226573D0 (en) *	1992-12-21	1993-02-17	Ici Plc	Heterocyclic compounds
US5998404A (en) *	1994-10-24	1999-12-07	Eli Lilly And Company	Heterocyclic compounds and their use
US5605908A (en) *	1994-10-24	1997-02-25	Eli Lilly And Company	Heterocyclic compounds and their use
US5665745A (en) *	1994-10-24	1997-09-09	Eli Lilly And Company	Heterocyclic compounds and their preparation and use
US5512574A (en) *	1994-12-21	1996-04-30	American Home Products Corporation	Quinuclidine and azabicyclo 2.2.1! heptane pyrazinyl ethers as muscarinic agonists
WO1997017955A1 (en) *	1995-11-13	1997-05-22	Eli Lilly And Company	Method for treating anxiety
AU1128297A (en) *	1995-12-06	1997-06-27	Eli Lilly And Company	Composition for treating pain
US6133253A (en) *	1996-12-10	2000-10-17	Abbott Laboratories	3-Pyridyl enantiomers and their use as analgesics
US6455554B1 (en)	1999-06-07	2002-09-24	Targacept, Inc.	Oxopyridinyl pharmaceutical compositions and methods for use
US20030147697A1 (en) *	2002-02-06	2003-08-07	Brady Patrick Richard	Evaporative desorption soil treatment apparatus and process
MXPA05001702A (es) *	2002-08-14	2005-04-19	Neurosearch As	Derivados de quinuclidina novedosos y su uso.
GB0220581D0 (en)	2002-09-04	2002-10-09	Novartis Ag	Organic Compound
US7418763B2 (en) *	2003-02-26	2008-09-02	Black & Decker Inc.	Hand vacuum with filter indicator
JP2009513491A (ja) *	2003-06-24	2009-04-02	ノイロサーチアクティーゼルスカブ	新規な８−アザ−ビシクロ［３．２．１］オクタン誘導体、及びモノアミン神経伝達物質の再取り込み阻害剤としてのその使用
PE20060437A1 (es)	2004-06-18	2006-06-08	Novartis Ag	COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR
GB0415746D0 (en)	2004-07-14	2004-08-18	Novartis Ag	Organic compounds
GB0521508D0 (en)	2005-10-21	2005-11-30	Novartis Ag	Organic compounds
GB0525673D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
GB0525672D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
ES2525076T3 (es) *	2006-05-19	2014-12-17	Abbvie Bahamas Ltd.	Derivados de alcanos azabicíclicos sustituidos con bicicloheterociclos condensados activos en el SNC

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US2640829A (en) *	1950-11-10	1953-06-02	Smith Kline French Lab	Isoquinolyl heterocyclic ethers
NL7109301A (pt) *	1970-07-15	1972-01-18
US4261990A (en) *	1979-03-09	1981-04-14	Ciba-Geigy Corporation	N-alkyleneiminoalkyl-dicarboximides as antiallergics and antiasthmatics
FR2531083B1 (fr) *	1982-06-29	1986-11-28	Sandoz Sa	Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments
GB8302483D0 (en) *	1983-01-29	1983-03-02	Beecham Group Plc	Compounds
ZA848275B (en) *	1983-12-28	1985-08-28	Degussa	New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring
DE3689974T2 (de) *	1985-03-14	1994-11-03	Beecham Group Plc	Arzneimittel zur Behandlung von Emesis.
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US4766215A (en) *	1987-02-27	1988-08-23	American Home Products Corporation	Histamine H1 -receptor antagonists
GB8718445D0 (en) *	1987-08-04	1987-09-09	Wyeth John & Brother Ltd	Pyridyl-ethers
US4843074A (en) *	1988-05-17	1989-06-27	Marion Laboratories, Inc.	1-azabicyclo[2.2.2]octan-3-yl 2-aryl-3-azacyclo-2-hydroxypropionates and their quaternary salts
DE3839385A1 (de) *	1988-11-22	1990-05-23	Boehringer Ingelheim Kg	Neue quinuclidine, ihre herstellung als arzneimittel und verfahren zu ihrer herstellung

1988
- 1988-07-29 CA CA000573471A patent/CA1307790C/en not_active Expired - Fee Related
- 1988-08-01 US US07/226,657 patent/US4929625A/en not_active Expired - Lifetime
- 1988-08-02 GB GB8818323A patent/GB2208510B/en not_active Expired - Fee Related
- 1988-08-02 EP EP88307113A patent/EP0306148B1/en not_active Expired - Lifetime
- 1988-08-02 DE DE88307113T patent/DE3887039T2/de not_active Expired - Fee Related
- 1988-08-02 ES ES88307113T patent/ES2061660T3/es not_active Expired - Lifetime
- 1988-08-03 FI FI883632A patent/FI94250C/fi not_active IP Right Cessation
- 1988-08-03 IL IL87329A patent/IL87329A/xx not_active IP Right Cessation
- 1988-08-03 AU AU20359/88A patent/AU605896B2/en not_active Ceased
- 1988-08-03 HU HU884077A patent/HU203348B/hu not_active IP Right Cessation
- 1988-08-03 DK DK434488A patent/DK170802B1/da not_active IP Right Cessation
- 1988-08-03 PT PT88177A patent/PT88177B/pt active IP Right Grant
- 1988-08-03 IE IE237588A patent/IE61026B1/en not_active IP Right Cessation
- 1988-08-04 KR KR1019880009927A patent/KR970002635B1/ko not_active Expired - Fee Related
- 1988-08-04 JP JP63197018A patent/JP2711272B2/ja not_active Expired - Fee Related
1990
- 1990-03-22 US US07/497,273 patent/US4997839A/en not_active Expired - Lifetime
- 1990-10-30 US US07/606,005 patent/US5082843A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE3887039D1 (de)	1994-02-24
IL87329A0 (en)	1989-01-31
DK434488D0 (da)	1988-08-03
PT88177B (pt)	1995-03-01
HUT48247A (en)	1989-05-29
ES2061660T3 (es)	1994-12-16
AU2035988A (en)	1989-02-09
EP0306148A3 (en)	1990-05-23
HU203348B (en)	1991-07-29
AU605896B2 (en)	1991-01-24
IE61026B1 (en)	1994-09-07
GB2208510A (en)	1989-04-05
KR890003753A (ko)	1989-04-17
GB2208510B (en)	1991-03-06
DK434488A (da)	1989-02-05
EP0306148A2 (en)	1989-03-08
IE882375L (en)	1989-02-04
KR970002635B1 (ko)	1997-03-07
FI94250B (fi)	1995-04-28
GB8818323D0 (en)	1988-09-07
EP0306148B1 (en)	1994-01-12
PT88177A (pt)	1989-06-30
FI883632A0 (fi)	1988-08-03
US4997839A (en)	1991-03-05
JP2711272B2 (ja)	1998-02-10
IL87329A (en)	1992-12-01
CA1307790C (en)	1992-09-22
US5082843A (en)	1992-01-21
JPH0193585A (ja)	1989-04-12
US4929625A (en)	1990-05-29
DK170802B1 (da)	1996-01-22
FI94250C (fi)	1995-08-10
FI883632L (fi)	1989-02-05

Publication	Publication Date	Title
DE3887039T2 (de)	1994-04-28	Azabicyclische Äther.
DE3850742T2 (de)	1994-10-27	Neue 4-Oxobenzotriazine und 4-Oxochinazoline.
US5434161A (en)	1995-07-18	Imidazopyridines as serotonergic 5-HT3 antagonists
DE69025621T2 (de)	1996-07-04	Heterozyklische verbindungen
KR102190087B1 (ko)	2020-12-11	트라이아졸로피라진
EP2386558B1 (de)	2014-10-01	CGRP-Antagonisten
EP2251339A2 (de)	2010-11-17	Verbindungen
JPH0631225B2 (ja)	1994-04-27	５−ｈｔ受容体拮抗剤として有用な新規ベンズイミダゾリン−２−オキソ−１−カルボン酸誘導体
DE69200290T2 (de)	1995-02-16	Thienopyridin -Derivative und diese enthaltende Arzneimittel.
US4873331A (en)	1989-10-10	Noradamantyl-carboxylic acid piperazinoalkyl esters
DE69215694T2 (de)	1997-05-28	Benzamid-derivate
DD282689A5 (de)	1990-09-19	Verfahren zur herstellung von trizyklischen amidinoderivaten
US4921860A (en)	1990-05-01	Quinuclidyl- and tropanyl-pyridyl ethers as 5-HT3 receptor antagonists
CA2091375A1 (en)	1993-09-13	Cinnoline-3-carboxylic acid derivatives
DE60208724T2 (de)	2006-11-02	Heteroaryl derivate als bessere liganden des nociceptinrezeptors orl-1
GB2131801A (en)	1984-06-27	Pyrazoloquinolines
DE69514315T2 (de)	2000-07-27	AZABICYCLOALKYLDERIVATE VON IMIDAZO[1,5-a]INDOL-3-ONE ALS 5HT3 ANTAGONISTEN
US5204470A (en)	1993-04-20	Azabicyclic derivatives
DE2624411A1 (de)	1976-12-16	Pyrrolotriazolopyrimidinderivate und verfahren zu ihrer herstellung
DE69324794T2 (de)	1999-12-02	Phenyl imidazolinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als 5-ht3-rezeptor-antagonisten
DE69320542T2 (de)	1999-04-29	Pyrrolothienopyrazin-Verbindungen als 5HT3-Rezeptoren-Antagonisten
EP2065386A1 (de)	2009-06-03	CGRP Antagonisten
DE3943180A1 (de)	1990-07-05	Cyclische guanidin-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
PT90437B (pt)	1995-05-31	Processo para a preparacao de derivados de benzo (di/tri)azinona
DD297815A5 (de)	1992-05-07	Ir-prismenspektrometer

Legal Events

Date	Code	Title	Description
1995-02-16	8364	No opposition during term of opposition
2006-06-14	8339	Ceased/non-payment of the annual fee